Pleasant Hill Homes with Trail(s) Available Amenities

Welcome to Pleasant Hill, Missouri, a charming community nestled in Cass County that boasts a vibrant school district and a wealth of amenities for families and outdoor enthusiasts alike. Known for its welcoming atmosphere, Pleasant Hill offers a variety of homes that cater to those who appreciate both comfort and convenience, particularly for those who enjoy an active lifestyle with easy access to trails.

The Pleasant Hill School District is renowned for its commitment to academic excellence and student development. With dedicated educators and a range of programs designed to inspire and engage students, parents can feel confident in the educational opportunities available. From early childhood education to high school, the district emphasizes a well-rounded approach, ensuring that students not only excel academically but also thrive in extracurricular activities.

For families who love the outdoors, Pleasant Hill is a dream come true. Many homes in the area are conveniently located near scenic trails, perfect for walking, jogging, or biking. These trails weave through picturesque landscapes, providing a serene escape right at your doorstep. Imagine spending your weekends exploring the great outdoors or enjoying leisurely strolls with family and friends, all while living in a community that values nature and recreation.

In Pleasant Hill, you will find a perfect blend of suburban tranquility and access to quality education, making it an ideal place to call home. Whether you’re looking for a cozy family residence or a spacious property with room to grow, Pleasant Hill offers a variety of homes that cater to your lifestyle. Come discover the charm of Pleasant Hill and see why it’s a wonderful place to live, learn, and play!

Newest Pleasant Hill Homes with Trail(s) Available Amenities

$1,100,000

Beautiful walkout, lakefront lot ready for your dream home. Life at Lake Winnebago has the feel of always being on vacation with so many community amenities. Basketball and tennis courts, walking trails, horse stables and access to the Arrowhead Yacht Club. Additional community information can be found at www.lakewinnebago.org. All docks must be approved and permited prior to the start of dock construction.

18 Checotah Bluffs Circle, Lake Winnebago

Listing courtesy of Dave Baldwin of Platinum Realty LLC.

$4,449,000

5 Beds ⋅ 4.5 Baths

Experience refined lakefront living on the private waters of Lake Winnebago in this exceptional custom modern craftsman by Walker Custom Homes—proudly prepared for Kansas City’s 2026 Artisan Tour. Perfectly positioned on a premier lot with a gentle slope to the water’s edge, this residence blends architectural elegance with resort-style amenities. Designed for both everyday comfort and elevated entertaining, the home features 4 bedrooms plus an expansive bunk room, including two luxurious main-level suites and additional bedrooms in the walkout lower level. Thoughtfully curated spaces include a private pocket office, full prep kitchens on both levels, a stunning wine cellar, and a showpiece wet bar. The lower level is truly next-level, highlighted by an incredible theater room, dedicated workout space, and seamless access to outdoor living. Step outside to your private oasis featuring a custom pool and spa, along with multiple covered decks designed to capture breathtaking lake views. Car enthusiasts and hobbyists will appreciate the suspended slab 4-car garage, complemented by a rare 5th rear garage door—perfect for lake gear and easy backyard access. Built on a 12 ft foundation, this home offers both scale and structural distinction rarely found in lakefront construction. No detail has been overlooked—finishes are truly over-the-top. Experience the relaxation of the lake views poolside, or enjoying the built-in hot tub. Bulkhead and dock anchors are already in place, making it easy to complete your ideal lake lifestyle. This is a rare opportunity to own a fully customized luxury retreat in one of the area’s most sought-after communities.

14 Tomahawk Circle, Lake Winnebago

Listing courtesy of James Asher of Asher Real Estate LLC.

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